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5 Beds
5 Baths
3,243 sqft

$1,245,500

105 HIGH STREET, CHESTERTOWN MD, 21620

Price per sqft$384.06
Built in1863
Property size3,243 sqft
Property typeResidential

Overview

Active

Active-bright

Listed Nov 7, 2025

Updated 13h ago

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

$8,286/mo

Est. mortgage payment based on a $1,245,500 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
MDKE2005890

Interior Features

Bedrooms
5
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.06 Acres

Other Property Details

Taxes
$20,218
Tax Frequency
Annually
Garage
Yes
View
Yes
55+/Senior Community
No
MLS provider logo

Listed by Coldwell Banker Chesapeake Real Estate Company
Listing Contact: 4434804275 

The IDX display contains information sourced from the Bright MLS, Inc. as of 9/22/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 9/22/2026 at 1:38 PM UTC

 

Benson & Mangold Realty

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